Tim Wilkinson: Making First Hire Product Managers Work

The average lifespan of a first hire Product Manager is 11 months. This is terrible for Product Manager’s and the businesses they join and then leave. What are the most common pitfalls that make this so difficult and what can founders and first hire Product Managers do to change this? 

Tim shares an approach to make first hires a success that is focused on product but contains plenty of insights for hires in other functions. He starts before the hiring process starts and then share some tried and trusted guidelines for founders and Product Managers to make the first 12 months in the role a case study in excellence. He shares some templates you will be able to use to set yourself up for better outcomes. 

Slides

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Transcript

Tim Wilkinson 

I’m gonna talk about the challenges of hiring your first product manager, which usually is in a startup space, that’s usually where I, where I kind of where I kind of work and come from. And, but there’s a whole load of stuff in here as well that, you know, if you’re from a larger organisation, or just hiring in general, that will hopefully be really useful for you. So I am, so I’ve worked in products for a long time, I’ve held kind of leadership positions VP, Head of Product positions at a number of LSA startups, I’ve been a first time product hire on two occasions, one occasion didn’t go very well at all. The second occasion went slightly better. So I’ve sort of been in this position from a candidate perspective. And I’ve also built product teams from the inside, in early stage startups and in and in large, large organisations as well. And now through through product heads. With the team here we help hire train and scale product teams in usually kind of fairly early stage and scale up companies. So obviously, it’s a real, it’s a real challenge.

Hiring from product for the first time, it’s only if you’ve never done it before. And in an early stage company, where there are no kind of structures and processes, and everything is still very sort of, you know, moving around and nebulous and all over the place. So the average lifespan, or the average life expectancy of the first high Pm is under 12 months, in an early stage startup, which is a horrendous statistic. Not obviously, for the for the candidates for people that join those companies. And then and then leave, it’s, it’s not good. And it’s also terrible for those for those organisations, it’s expensive. And the kind of figure is somewhere between 150 250,000 pounds, it would cost to hire somebody. So that is that is lost. Once they once they’ve left, that that’s kind of all costs included. So you know, people’s time, obviously salary and on costs. Many recruitment fees, you’re paying all of those kinds of things that are bundled in, plus opportunity costs, right. So obviously, for startups time is the absolute is that is the you know, is like is the most valuable thing. And if you if you lose 1112 months, with somebody not performing in the role, you know, there’s opportunity cost missed there, where you could have what could have happened if you’d have kind of hired right and got the right person in damaging for the rest of the team, potentially, you know, wrong move, disruption and all that sort of stuff, which which can cause kind of ramifications for the rest of the team, the rest of the organisation. And as I said at the start, it’s, you know, really crushing for the pm who, you know, in other circumstances, may well have thrived. So this is this is not necessarily about somebody being a bad PM, it’s usually about kind of fit and making sure that, you know, the business knows why they’re hiring. So in order to make that, that, you know, the sort of impact that you can have, in order to have sort of making that hire work, as best as possible, really, really starts very early on in the sort of decision process of, you know, I think we need to hire a PM. And you can influence all the way through that hiring process and through through onboarding. And then obviously, obviously, throughout their tenure, but that that early stage is really, really critical in terms of getting them getting it right and getting them embedded in your company correctly. So what I’m going to talk through today, is talking about when to hire, so if you’re really early stage company, when might you think about hiring your first PM, what you might look for how to prepare, both as a hiring team and as a candidate. So throughout I’m going to try and give sort of both, both viewpoints really from from a company perspective and the candidate perspective, what a good onboarding could look like first 3060 90 days and then and then we should hopefully have some time for q&a.

So when to hire your first product manager. So the kind of the simple answer of this is is theoretically when you have product market fit or some some sense that you have product market fit prior to that point, generally, the founding team you know should be pretty small for for most companies, and absolutely focused on building a product there is nothing else until you haven’t product that people might be interested in, there is a real danger actually of scaling too quickly. Because you, then you then have a whole load of inertia in the organisation, it’s really difficult if you’re, if you’re pivoting, you’re changing the product, trying to keep everybody up to date. And, and focus becomes very, very difficult. So you really want to keep the team as small as possible until you’ve got some level of certainty that the thing you’re doing is right, and that the thing you’re doing is, right. So once you get to that level, and you’ve got products in the market, and you’re starting to get, you know, customers using the product, you’re starting to get customer feedback, you’ve got, you know, lots going on around the product. Two things happen, a the founder CEOs job changes. So when they were focused on product, they now have to start thinking more about the rest of the company. And also the workload, just just gets, you know, material large, materially larger. So it’s very, very difficult for that for that kind of one person to take on all of those things. So it starts to make sense, then to hire somebody to help look after product. With you. Before that point, again, the sort of the sort of latency that you’re adding by bringing in a PM. And the sort of cost of that isn’t, isn’t really worth it, you want to keep that, that connection between customer and you and the product as tight as possible, really.

But then you also as a sort of co founder, have to face a whole lot of challenges. So there’s a changing nature of of your role, and you’ve got, you’ve got this thing that you’ve created your baby, and you’ve got to potentially, you know, you’ve got to think about how you might work with somebody else to take that on to the next stage and the next steps. But there’s a whole thing there about kind of letting go. And, and also focusing your attention as the company becomes your product, rather than the product itself. Lots of different demands on attention on your attention. And then obviously, line managing and working with a PM, and you may not have done that before. So a lot of a lot of founders haven’t necessarily worked with, or worked with a product manager before, and they suddenly line managing this person. So that’s, that’s a real challenge. And then for a product manager coming into an organisation in the first as a first hire PM, obviously, building credibility with the CEO and the organisation is really difficult. Being able to push back and challenge some of the ideas and assumptions that might have might, you know, just just be there already, is very difficult, particularly that person is your, your boss, and your line manager is really challenging. Having autonomy can be a challenge, obviously, it was part of that transition from, you know, somebody owning the owning the product entirely to them, letting somebody else take hold of it, it’s a real, it’s a real, it’s a real challenge. And then obviously, working under somebody who is still learning their role, and as you know, to the, to the challenges of the CEO is still learning, like how to work with a product manager, what does the product manager do? How can they help me. So it’s a really sort of messy space. And, and the, the key thing to do is to is to just spend some time really thinking about it. And a number of companies hire product managers potential because they’re told to write sometimes they’re, you know, they’re bored, and they’re, you know, they’re VCs, their investors might say, actually, okay, now you’ve got a bit of product market fit, you need to start thinking about hiring. And so they kind of go out and hire and don’t really spend enough time really thinking about what this person can do and how they can impact the organisation and help them.

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So, so the first thing to say, when you when you sort of start that journey, really is that, that hiring a product manager is a team sport. And that and the reason is because, you know, for those of the things in product, know, the role touches all parts of the organisation, and to be successful, you’ll need to interact with a number of different people around the around the organisation, depending on depending on the scope of the role and the stage of the business and all that sort of stuff. So it’s not something that can be done in isolation. And, and one of the, one of the best ways of making sure that, you know, when you’re when your first pm actually starts, they are on a good footing is to involve other members of the team in in sort of varying levels of inclusion. So, so for some people, you know, they might just need to be informed, they might need to know what’s going on and have an opportunity to engage if they need to. And for others, they might need to be you know, very involved in the process have had you know, veto capabilities. So, so, again, it kind of depends on the focus and the role that you would want somebody from engineering for example, the senior person in engineering for example, involved at some point To, you might need somebody from from marketing, you might need somebody from sales, you might want somebody from CES, again, depending on depending on the focus of the role and where the challenges are in the organisation. So it’s worth kind of taking a step back and just thinking about, okay, who needs to be involved in this. And then a bit later on, you can kind of decide because you don’t want a tonne of people because that will, you know, that can cause friction. So later on, you can sort of start to decide, okay, who do I just, he just needs to be informed, and included versus who is critical and needs to be part of the part of the process. In terms of who you might hire product managers, again, so we’re gonna, we’re gonna go through a skill sheet in a second. And we’ll kind of start to talk about the, you know, the different skills and biases, there are some, there are some sort of fairly standard things that you might want to look for, again, depending on the size of the organisation, Jonathan Goldin, who was who was director of Airbnb first, I think some time ago started talking about pioneers, settlers and town planners, as a way of sort of articulating the different personalities that work well in different in different environments. So pioneers are people that are really happy with with ambiguity, they like the challenge of sort of creating something from nothing and bringing something new into the world. And then obviously, very good in in kind of startup environments, may get frustrated and struggle in slightly larger, larger organisations, that lives are more about scale. So they want to take something and grow it. And then town planners are people who can, you know, make something robust. So if you sort of, if you sort of overlay the sort of typical journey of a product over the top of that, where you have that sort of very early MVP, changing a lot, yeah, over over racial short period of time, and then that moves into, okay, we’ve got something that we think our customers like here, how do we scale that out to a wider audience? And then it becomes okay, how do we how do we make this more robust and build it for the long term? So, so those three, those three kind of roles, or those three sort of personas map onto those three areas, if you’re hiring for, again, if it’s if it’s a really early stage startup, it’s not great to hire somebody, for example, who is only worked in a large organisation is more of a town planner mentality. And the reverse is true. Often people think, you know, if I hire somebody, that’s that’s been a been a pm at Amazon, they can bring all of that knowledge and all of that value across. But often it just doesn’t work out that way. Without the infrastructure and the things around them to help them. It’s not, obviously we’re dealing with people. So it’s not, it’s not a hard and fast rule. But it’s usually good in the firt in the really early stages, to have somebody who understand the messiness of first situation that they’re going to that they’re going to join. And then, and then on top of the sort of specific, specific skills, there’s some sort of must haves, good, good to have some bonuses that are worth kind of trying to pick out. So some of them are fairly no brainers, right? Good intellectual ability processing and simple synthesising information. And communication is a really big one for product managers demonstrating leadership, even if they’re not in a leadership role, because often, certainly, in early stage, companies, they have to be able to show leadership and influence. And then And then obviously, be be collaborative, and effective within your culture. I think I think he’s good to have so I mean, that’s a bit of a, you know, knack for knowing what users and customers want. If we all had that, then then life would be a lot easier. But certainly strategic and analytical background. technical background can be helpful, it’s not required. Candidates always speak to me and asked me Do I need to have a technical background? Or do companies prefer me to have a technical background? It really depends on the on the on the role and the organisation. And we’ll talk about that in a minute when we get on to the kind of skill sheet because it may be that actually a UX background or a marketing background is is is more valuable. So that’s that this is a this is a list from from Todd Jackson, who who’s it’s switch and Dropbox and again, these are I think these are just good to have. They’re good to kind of think about as you as you start thinking about the kinds of skills that your that your Pm might need to have So the really important thing is to sit and and try and understand exactly what the pm persona is that you’re going to need to help your company achieve what it needs to achieve over the next 1224 months. It’s not a good idea to just kind of cut and paste and think, Okay, this is what a product manager looks like, we’ll just hire for those for those things. You need to really stop and think about, what are the goals and challenges that your business faces? What are the team’s strengths and weaknesses that we currently have? So where are we, you know, where do we have depth? Where don’t we, and then mould that together to think about, okay, how can this person come in and contribute to the team. And it sounds quite obvious, but it’s amazing how many how many companies don’t do this. And again, doing it as a team. So working through these these things together as a hiring team, is really, really important. Because as an individual, you will have blind spots. And so doing it as a doing it as a group. And having a good discussion, helps to identify those, those blind spots helps you to have a really good good discussion about about exactly what the business needs. And again, when the pm starts, everybody, all of the stakeholders will be aligned about why they’re there and what their job is going to be. Once they’re once they’re in position. Once you’ve kind of thought about those things, and you I mean, you may already have those things, right, if you’re, if you’re doing a good job, you may already have an idea of what you’re, you know, what your quarterly half year yearly goals are, you may have a really good understanding of what that timeline looks like, not necessarily in terms of, you know, kind of features and roadmaps and all that kind of stuff. But you may have a good understanding of what that looks like in terms of the commercial goals and where you need to get to what’s a really good thing to do is to sit down and write do some creative writing, and sit down and write an appraisal, essentially, an annual review for the person, you know, for this Pm one there it once they’re in place, if you before you sort of start talking to candidates, and really just get creative and think about what would they have achieved? In an ideal world? What would they have achieved over the over the sort of 1224 months that you want them to be in the role? What metrics will they have moved? How will the product be different? How will the organisation be different? And then share this with the hiring team, right and start to have that discussion about, okay, do they agree with this is this is this kind of accurate, and that document can start to form the basis for other collateral that you might need, like Job specs, and job ads, and all that sort of stuff.

Tim Wilkinson 

So once you’ve got that kind of background, and that sort of basis, you can start to work through skills, A skills matrix, you can put your own skills matrix together. Or, as Kurt said, at the start, there’s a version on Google Google Docs that you can you can borrow from from us. And essentially, it’s a list of all of the skills that a product manager might have, with a definition so that everybody involved can, you know, clearly understand, you know, what’s meant by those skills. And you can sit and stack rank, though, stack rank those skills, doesn’t mean that they don’t need to have so. So please, a couple things. First off, no candidate is going to have absolutely every skill on that sheet. And it doesn’t mean that if you if you don’t choose, you know, whatever it might be commercial understanding that that isn’t a valuable thing. It just means that it’s not as valuable as the as the as the top five, for example that you that you might choose. So you can really start to identify what are the priority skills that this person you think this person needs based on what the business needs to achieve, what impact they’re hoping to have, will need in order to be successful in the role. And then you can use this throughout the process. So when you when you download that sheet, you’ll see that it’s got, it’s actually got a scoring Scoring Matrix on it as well. So for everybody involved in, for example, interviewing processes, they can score a candidate from zero to three or zero to five for each of those top five skills. And then you can say, Okay, so for, you can set a benchmark so so top five skills are table stakes. Candidates must go well on these in order to progress and you can set a minimum score that you’ll you’ll accept. So it gives you a standardised way of benchmarking candidates for a start so that you can actually in some sort of scientific way actually kind of measure and track appropriately attract candidates and measure candidates against each other. But it also gives you a load of great content content for feedback and helps you structure. And we’ll talk a bit in a second about about sort of candidate experience. And actually being able to give good feedback is really, really important for candidates who take them forward. And candidates you’re not, you’re not taking forward. And it helps you in other rounds to decide what to dig into. So you might see that actually, you know, a candidate was good, they passed the top five skills in that in that first interview, but maybe they were a little bit weaker on some areas. So you might want to dig in and get some get some better understanding in those in those areas. So they can just provide a really good framework for the for the rest of the process. So for candidates, and so thinking about it from the other side, now, as a business, having those things in place, and really understanding why you’re hiring is critical. Obviously, then, you know, the skills that you’re hiring for, but also as a candidate, what you should be doing as a candidate is really checking that the companies you’re interviewing for, understand those things. It is all too common for candidates to land at a an early stage company and not and find very quickly rather, that the company doesn’t really understand what they want you to achieve. There are no clear goals for for your role, and you’re just sort of, you know, dropped in and told to crack on. So as a candidate, you want to really test that with the organisation, it’s part of your due diligence, do they know why they’re hiring a PM? Do they know what success is going to look like, so that I can understand what success is like as a candidate, I always kind of think, for for a PM, the job almost starts in the hiring process, trying to identify what success looks like, and and then diagnose the organisation kind of as you as you go through that process. So it’s really good to ask every single person that you get a chance to speak to, are they aware? Do they know what the mission is? Do they know the OKRs? Do they understand, you know, what success is going to what success looks like? Because, again, if there’s misalignment there, there’s, you know, that’s a red flag in terms of in terms of the organisation. The second thing you want to do is be really clear about

Audience Member 

Yeah, sorry to interrupt you. So you’re changing topics, and I had a question is okay. Yeah, so you’ve been talking a lot about, like, metrics for a product manager, but I’m wondering, like, for a product manager, what are, you know, reasonable metrics to expect? So, you know, running a company and be like, alright, like, I want to increase revenue. But that’s not something that should be like, you know, I expect that product manager to do I expect him to influence it. But maybe that’s not a fair way to measure performance. So my question is, like, in your experience, what are some of the best ways to measure success? When it comes to product management? Is it like softer things like delivering like certain product improvements? Or is it hard metrics, like reduced churn? Or, you know, those those sorts of things?

Tim Wilkinson 

Yeah, that’s a really, it’s a really great question. And the answer is, again, it’s a bit of a kind of, it depends. Depending on the stage of your stage of your organisation, you can certainly have hard metrics, and you know, reducing, reducing churn, improving customer acquisition, all of these things could be part of, yeah, part of part of a metric. Again, it as I say, depends. So yeah, it’s kind of ultimately kind of look across the product, understand what the challenges are, and, and identify those things, but there may well be, there may well be more softer challenges that the organisation faces, right, they might have, like, just delivery challenges. So So there might be issues around, yes, you know, speeding up, you know, maybe we’re deploying, you know, once in a blue moon rather than regularly or, you know, so they can be some really hard and fast thing. So it just depends on what challenges the organisation is facing. But it’s a great question, and it’s a good thing to think about. So I was mentioning in the slide of adding some creative writing is think about what some of those metrics might be, and whether they can whether they can influence those things. If not, they can I mean, if you Yeah, again, things, some of the commercial metrics, they might be involved in influencing, and there isn’t. You know, so you, they could be a part of that team that is helping to influence those things. So really depends on the business, and the challenges that the company is facing. Thanks to. So, so then, yeah, for a company, next thing you kind of need to start looking at is thinking about how you define your process. candidate experience is really really important, as a as a candidate, you are looking to understand whether the company is as you know, got it stuck together, right? Can they this point, you know, nothing about the company. And it’s really important as a as a company to, to recognise that and empathise with the customer, I think the Windecker with the enterprise, with the customer with the candidate, because it’s often easy to forget that you know, everything about your company, right, you think your company is great, and it’s gonna go on and do fantastic things, the candidate has no idea of any of those things they’re meeting you for the first time. And so actually, some of the really simple things are the things that they will, that they will judge you on. So if you’re not getting back to candidates quickly, if you’re, you know, if you seem disorganised, if you’re adding in new stages to the process, you know, ad hoc, all of those things can kind of affect the candidate experience. And, and that’s all they know, of you, it’s a bit like that, you know, first impressions thing. So it’s really important to get these things sorted out. And, and, and, you know, be really well organised around this stuff, get feedback quickly, give feedback really quickly, have as few stages as you can get away with, but you obviously you need enough to be able to do a proper assessment. But, but you know, you need to keep the stages, you know, short, so you can get people through the process quickly. And then get really organised internally in terms of like lining up everybody who’s going to interview and all that sort of stuff. When when you know, when you have an interview scheduled, and somebody and it has to be cancelled, because somebody says, Oh, you know, something else has come up from the candidates point of view that saying, you know, I’m not that valuable, this isn’t a priority for you, there are other things that are more important. Obviously, you know, life happens. So it can’t always be avoided. But it’s really important to just just kind of get as organised as you possibly can on on those things. There’s a load of really good resources on what a process can look like. I didn’t put it in here, because it would just just kind of take too long to go through. There’s lots of questions about, you know, exercises, know exercises, send home tasks, in interview tasks. And we can maybe talk about some of those things in the, in the, you know, the Q and A’s. But the key thing is to keep it punchy and short and push people through the process quickly and efficiently. So so from a company perspective, what winning looks like is having a really clear understanding of what the pm needs to achieve over the next 12 to 24 months, having stakeholder buying an alignment, have a clear scoring process, a standardised scoring process and methodology that’s easy to administer. A great candidate experience with engagement all the way through the process and, and as much tighter you know, as the shorter time for hire as possible, while still getting the balance, right, that you’re you’re you’re covering up all the bases, and you’re giving yourselves enough opportunity to properly assess the candidate. And then from the candidates perspective, you really need to do your due diligence, particularly for those really early stage companies. So does anybody in your network know that company? Can you talk to them about them? Can you find out more about them next, you know, from the outside? What does their runway look like? You know, how are they doing for funding? What are their customers? Do they actually have, you know, are their customers kind of valid customers? Often with early stage b2b, they might have a number of customers, but those customers could be on trials or they could be invested sometimes. So it’s really important to try and tease out exactly what stage they’re at. And really understand the real challenges that they that they face. What you know, I think as a candidate, you can’t ask too many questions. You should always be asking questions, a so that you understand exactly what you’re getting into. But be because that demonstrates to the interviewers that you have interesting curiosity, which which are key key product management skills, but ultimately you’re looking for for openness and honesty. So so everybody that you interview, or you’re interviewing with shouldn’t be really open and honest, they should understand and own the problems that they that the organisation has every organisation, every startup has problems, that’s fine. And but they need to really understand those. Oh, sure. Anyway, not sure what’s happening there. Oh, yeah. Okay, so. So just before we move on, do not tie as an early stage company do not hire a head, VP, Director of Product as your first hire. There’s a couple of reasons for it. So it’s easy to kind of think, Oh, well, we’re not really sure. So let’s hire somebody who is really, really kind of senior and experienced, and they can kind of come in and they can tell us, it really often doesn’t work. And there are a number of reasons why a head of VP director is beyond generally is beyond the IC, the individual contributor stage, they are, they will want to be building out a team, they’ll want to be working on strategy, they will want to be doing things that you’re probably not ready to do yet. More than likely your first hire RPM will be essentially an individual contributor, this happened to me in one of my first roles I was hired in as a VP of product, I was the only product manager in your organisation, I was just doing product work, right. The second thing is, you probably aren’t ready to relinquish control entirely. So you probably want to have an, you know, the option to be able to direct this person to some degree. And a head of VP, really senior person may well struggle with that. So ideally, you want to find somebody who is senior enough and experienced enough, but he’s still prepared to work collaboratively with you and take instruction. And, and yeah, and happy to get into the weeds and do an individual contributor role. The other thing is he wants to give yourself optionality. So there’s a good chance that this first hire, even if you do all of these things won’t be right for the head or VP, director role. If you’ve never worked with a product person before, you know, until you’ve worked with somebody, you might not know what you need in that role. And the organisation will look very different at the point at which you need to hire more product managers and need to hire a head over to VP. So this person might be promoted into that role down the line, but they might not. And it’s always a sort of, it’s always a red flag, when you look at a start up, and you look at the org structure. And there’s a whole load of mess at the top there where they’ve got, you know, Vice President, senior vice presidents and all that sort of stuff. And it’s usually because they’ve hired too senior too early. And it can end in disaster. So so my my advice is always hire a midway or a senior PM, give yourself optionality. And then you can either promote them or you can hire above them later on, if you need to. And then finally, in terms of we’ll move on to the we’ll move on to the the kind of onboarding and second, but just just to sort of finish out the time process. Don’t make it hard for somebody to accept your offer and move on to the site, because that’s in my office is blinding me, so give me one second. Yeah, so the other thing is, don’t make it hard for somebody to accept your offer.

Tim Wilkinson 

Sadly, this is where a lot of things fall down. It’s just I mean, it’s a general kind of recruitment thing, but you know, clearly list out the offering an email, give them full details of the package, show what benefits and perks there are, don’t get across if a candidate negotiates. This, this does happen quite a lot where founders get a bit offended if a candidate negotiates I’ve seen founders get upset with so often you get package in stock. And and I’ve seen candidates actually I’d rather than sorry, salary and stock I’d rather take salary than stock. And and, and founders get really upset because they think you’re not you’re not invested in the company. Because you’re not taking because you’re not taking stock. Again, just remember that this person knows nothing about your company, you think your company is fantastic. But this person’s interviewing at three or four other companies where the founders think the company is fantastic. They don’t they don’t know. So so. So yeah, just just be aware of that, and then don’t have unreasonable terms in the contract. Again, just you know, it’s again, it’s about candidate experience, and to some degree trust. And this, again, is why it can fall down because if this process isn’t managed, well, essentially two people who have only just met are starting to chip away at trust before they’ve even started in the role. So really important to get that all sort of sorted out and aligned. So this is brilliant, you know, you’ve hired a fantastic product manager, you’re both really excited. And and it gets to kind of day one. And, and onboarding. Onboarding has such a huge impact on somebody’s likelihood to succeed and stay in a role. So there’s, there’s evidence to show that it has a 50% impact on New Hire productivity, and massive retention gains beyond two years. So it’s really, really important to get the onboarding process lined up really well, as well. The simplest thing is to make sure you have a plan. And unfortunately, so many people don’t have a plan. So somebody turns up, you know, you hear stories of people not even having laptops and things on the first day, but they kind of turn out and then it’s kind of winging it from their jobs done, right, we hired somebody really not the case. So you can have a really detailed first 30 day plan. And actually, what I tend to do is use something like Trello, something really simple, like Trello, to list out, you know, first day, second day, or first week, tasks that they can be doing sometimes really basic and mundane. And, and again, for candidates, some of the really simple things that you don’t think about, like, you know, what should I wear, or who do I speak to about holiday really basic stuff, you can list out on a on a on a Trello board. Again, if you’re an early stage company, you’ve probably not done a lot of hiring. So you probably don’t have these resources, you don’t need to have all the resources of a big organisation, you can just get something really simple, you know, generated that just helps to take some of those questions away. For a product manager, really, the first week and first 30 days is about learning, you shouldn’t really expect them to be contributing much in that first 30 days, they might start to do a few little things. But the key thing is to have them learning so get them meeting key people around the team. I always think it’s good to ask, you know, for them to ask the same three questions, right, what’s going well, what’s not going well, from that person’s perspective. And then what’s the one thing they could start doing that would be helpful, it’s a really good way of them starting to understand the organisation, get to know people and start diagnosing where they might be where they might be helpful. Get them to learn the product. They’re shadowing, you know, customer success, if you’ve got customer success or sales, have them sit down with a CTO and senior engineer, get to know them, get to know the product, review documents, and they can even contribute to them right they can, they can start tidying up or generating documents is a great way of of learning about the product. That’s kind of you know, potential client facing docs helped us docs and support docs, things like that. And obviously read up on product strategy and goals and discuss it with them, you should really be meeting with them as their line manager in that first week for a quick, you know, even if it’s 15 minutes every single day at the end of the day. So just check in and understand, like, you know, how it went who they spoke to what they’re learning, you can start to reduce that, you know, after that sort of first and second week, but but meet within every day, have an end of first week wrap up. So that you’re really getting a lot of contact time with them and starting to starting to build that relationship on both ways, right, and both sides. Give them a project to do but don’t throw them into something complex. So so it can be quite good to put them in a team, getting them shipping something with a really low risk factor. But something where they can start to learn the product. And they can start to learn the personalities and the technology and how things are done. But again, really low risk, it could probably be done without their involvement. But it’s something that they can start to feel like they’re contributing to the organisation and getting getting stuff shipped. And then throughout that 30 days, you can start to work collectively on a 60 and 90 day goals and 60 or 90 day plan that they can start to work for. And that’s a good way to have them think about the organisation and the and the product. Obviously, if you’ve if you’ve done all the work early on, and you understand what it is that that you want them to achieve, then you can talk through those and and you can start to put a plan together about how they’re going to go about doing that and work with them really, really closely on it. Okay, so So that’s, that’s everything. I hope that that will sort of help to make sense. And again, there’s there’s lots of stuff that’s transferable to larger organisations as well. There’s a few there’s a few references that are worth picking up. So Ken, Ken Norton, I’m sure a lot of you will know he’s done a really great blog post. went about kind of when to hire your first pm There’s a good book called cracking the pm interview, which is written for product managers. But I think it’s really great for hiring managers to have a read through as well, from their perspective. And there’s another there’s a great book for leaders, which which you may have come across called first 90 days by Michael Watkins, which is about really about senior leaders coming into a business and and how they can be successful in their first 90 days. But I think, because product is such a broad role, I think it’s a really useful read for product managers as well.

Tim Wilkinson 

So questions, thoughts, comments? A practice? Is that right?

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Mark Littlewood 

Right, Ryan from Point of Rental.

Audience Member 

Hey, there, thanks so much for the talk. Just two questions. First, around compensation. In, you know, every every type of role, there’s kind of I feel like generalise temperaments of, you know, where they’re gonna want. They’re okay with a lower than market salary for a big chunk of equity or vice versa. What do you see with product managers as being the most compelling compensation packages to get the best people in for, you know, your first pm hire? And then secondly, what are some red flags to look for over the first? I don’t know, 90 days to a year where it’s, you know, you said most of the time, the first hire won’t probably end up working out, what are the kinds of things that you should be looking for? Because obviously, the quicker you can move on to the longer term hire, the better but you also, yeah, you have to give people a chance and stuff. So I’m just curious, your thoughts on those two things?

Tim Wilkinson 

Yeah, there’s, those are two great questions. So so. So the compensation, in terms of that mix of kind of base salary and equity? I find it varies depending on depending on people stages of life, actually. And, and also, there, they’re there, to some degree, their appetite for risk. So I’ve certainly found that that you find people who are who would much rather just take a salary than I mean, they’re happy with equity, but they’d rather than wait was more on the salary. Because they, you know, there might be the primary breadwinner, right, they’ve got bills to pay. And actually, the, you know, the cash right now is, you know, is frankly, what they need, rather than, you know, they’re not necessarily in a position of having a luxury of essentially investing to some degree in the company, or

Mark Littlewood 

they might have worked for equity before.

Tim Wilkinson 

Exactly. Yeah, exactly. That was exactly right. So that’s what I mean, you know, where they, where they’ve maybe been on that journey before, they may be kind of a bit more. Yeah, a bit more, you know, a bit more sort of wise and kind of thing, actually, you know, how’s this gonna work, and I would rather, I would rather take equity, or sorry, I’d rather take rotate salary. Again, that’s why I kind of, but the broader point is that there are lots of different things that motivate people. And salary isn’t isn’t necessarily the main thing. Particularly with product folks, the team, the opportunity, and the type of product, they’re working on the you know, the excitement of the market, or the or the product is really, really important. So, so even though, at the moment, for example, salaries can be a bit crazy. It’s not, it doesn’t always come down to salary. There are some other factors as well, that influence it as well. I mean, it’s, it’s not uncommon. If you do end up negotiating, it’s really important to have a really good discussion with them to understand what are the things that that are important to them, for some people a bit more holiday is important to them. And they will take, they will take another two or three days holiday because they’ve got family abroad, for example, and they’d like to visit long weekends, over five grand, over five grand extra in their pay packet, for example. So So I think on salary, it’s really, really important to, to understand what it is it’s motivating the person that you’re talking to. And again, that’s why it’s really important when you when you make the offer to really list everything out and go through it with them. Either you or if you’re you know, if you’re using a recruiter go through it with them to really understand you know, what is important to them, pension might be important to them. Again, with benefits that changes depending on life stage, right, younger people might really be interested in gym membership. Somebody else might be more interested in travel to work vouchers or it’s all these things. It’s the complete package. I suppose I’d say it’s interesting. When and then and then Sorry, go on.

Mark Littlewood 

To answer I’ve got some questions lined up, but I’m just picking up on your issue about negotiating with recruiters. Should you ever do that? Considering a recruiters are generally compensated by salary, so they’re less likely to communicate fairly things like I’d rather have more holiday. And shouldn’t you actually be talking to somebody directly at that point?

Tim Wilkinson 

Yes. So that yeah, so that the the advice I want to get back to the second question that was asked, which I’m doing, say I needed reminding on it, because it was a really good question. But I’ll answer this one and then come back. So well, two things. First of all, if you’re if you’re using recruiter, you should have trust with them. So you should build up a relationship with somebody who you trust. And and he’s able to, and you know, he’s able to do a good job and isn’t just in it for that kind of, you know, isn’t it for the long term relationship rather than that, that kind of shorter, shorter payoff? One of the areas, one of the areas that recruiters can be really helpful in is informally floating and offer? Yes, I’m sure there are sort of unscrupulous people out there. But if you have that really trusty, trusted relationship with them, they can be a really good conduit, that understanding some of the things that we’re talking about so so they can speak to a candidate initially and say, Look, this is what they’re thinking of offering, you know, how does that sit with you? And, and so that when you get into that, when you make the formal offer, you’re much more sure about how it’s going to land. But also the recruiter should have had a conversation with the candidate to understand what what are those factors that are important to them, so they can help to advise in terms of what that offer looks like? So I get, you know, the question, I think that’s a it’s something that everybody thinks about. And it’s really important, I mean, I agree, have those conversations as well directly if you want to, but, but a good recruiters should, you should be able to trust them. And you should be able to work with them to do that. Because they’re ideally, they should be more motivated on continuing to have a relationship with you, and continue to work with you. And

Mark Littlewood 

they’re all uniquely not like the other recruiters, which is great to hear. So Brad, next question, then Joe, then Mark Stevens. So, Brad,

Audience Member 

thank you, Tim, this is very helpful. As the company is starting and growing, or even a company that may be older, but it’s reaching a point of critical growth. These product manager roles are the first ones often expected to be kind of combination strategic product management and execution, Product Owner responsibilities together. And if so, then how do you know at what point to have a dedicated product owner role to free up Product Manager for really strategic work?

Tim Wilkinson 

It’s a really great question. And and, to some degree, it depends on which school of thought you come from. So I could be, you know, there’s obviously a whole debate actually raging at the moment about whether whether a product owner is a you know, in a, in a smaller in a smaller tech company, is is something that needs an individual specifically to do that role. So I think, yeah, so So, so just, you know, kind of thinking through. I mean, personally, I’m a, I’m a fan of having a product manager, try and do the end to end. So. So even if they are thinking strategically, which, which they should be doing, I think, I think my my preference would always be to, you know, have have discrete teams that are focused on particular areas of the product. And then a PM, who is working directly with engineers, if you’ve got a really strong engineering team in this, they can take on some of that, you know, Scrum Pio role, and, and give the pm a bit more time to be thinking about some of the strategic stuff. So, yeah, good, good question. The other thing actually, I’ve seen is project managers sometimes as well. So I have seen seltos, really, you know, kind of scale ups, be really successful with project managers, who are essentially just managing the flow of work through the engineering team. Okay, thank you. 10.

Mark Littlewood 

Great, and I think that probably segues into Mark’s question, but let’s go with Joe first.

Audience Member 

Oh, Mark, if you want to go first, that’s fine with me, segues. Okay,

Audience Member 

so my question is sort of related in that I have a 12 person development team with multiple products. So we’re not the size where I have a desk that has product manager on it. But we are at the size where I really, as the founder don’t want to spend my time managing any of these products, because my focus is on the company in the sales. Yeah, so I wondered. So the solution we’ve adopted so far, essentially, is to have a one of the developers, senior developers and sort of product lead on the product. But I wanted to drill down and understand on whether what your thoughts were on how this alters the equation and what your thoughts are.

Tim Wilkinson 

Well, so without without sort of being obviously, I don’t know that that person in the in the character, there is a risk that so obviously, we all know that the PMs role is to balance a number of different parties, right? It’s to is essentially to negotiate between a number of different things that are in tension, right? What’s right for the business, what’s right for customers, what’s right, from a technical perspective, if somebody is if somebody is too wedded to one of those areas, then you end up with a bit of a bias. So there is a risk that, you know, if you if you, you know, if you kind of use a different situation, but if somebody from sales, took on a product role, then there is a risk that they would have a bias for obviously, just doing exactly what the customer wanted all the time. Which isn’t a great, which is obviously a great way to build to build a product. Because it might not be useful for the, you know, might not be commercially viable, for example. So my sense is that the person or product role needs to be needs to be an independent arbitrator between those between those things, which is why I always think that a pm should report to the CEO and not to the CTO, for example. Because because that’s the you know, otherwise they again become biassed because their line managers and CTO, so I don’t know, did that help? Mark? Does that answer your question? Yes, I think Do you think it’s possible for somebody to be a part time pm? Or do you think that’s inherently contradictory role? No, I don’t think it is possible. No, I don’t think it’s possible to be a part time pm.

Mark Littlewood 

Thank you very much. Part time pm within the organisation. What about kind of, I mean, these are pretty relatively common things, fractional. Fractional CEOs, CMOs CTOs, there’s a there’s a whole I mean, this fairly established stablished thing. How do you? What was your was your kind of thinking on? You mean,

Tim Wilkinson 

in terms of see, like, see PTOs, that kind of thing where they’re sort of doing two hats?

Mark Littlewood 

No, I’m thinking about if product is something that you really need, if there’s one person full time in an organisation, and you say, Okay, you’re full time in the organisation, and two days a week you’re doing product and three days, you’re doing something different. There’s always going to be tension, but there are organised that older individuals, and I think you do some of this as as well, who will work maybe one day a week for an organisation over a period of time to help guide some of that? Yeah,

Tim Wilkinson 

I think yeah, I mean, I think that’s possible. But I think the scope has to be very clearly defined. Because I think otherwise, yeah, it becomes, I think you have to really understand what value that person is has gained, you know, yeah, is there like it has to be really targeted in terms of what they’re actually doing what and what they’re contributing, most, most product managers will say, they will say two things, they don’t have enough time in the week to be doing all the things they need to be doing. And they really struggle between the strategic and the. So the sort of three things of strategic, the the sort of down in the weeds implementation, and then also the management kind of part of it. So there’s a real challenge with PMS, in terms of how they spend their time between actually having chunks of time where they can be creative, where they can build and make things and then chunks of time where they’re doing management meeting you type stuff. So So then, if the role is either part time or or split, the pressure just becomes even more acute. So I think you have to be really clear in terms of like, what they what their primary purpose is during that period of time.

Tim Wilkinson 

Is that all helpful? Mark

Audience Member 

that It’s very helpful. Thank you. I think in all our jobs, there’s constant risk. That’s why we’re in. We’re in this business is.

Mark Littlewood 

Joe pitch?

Audience Member 

Thank you. Thanks, Tim, you said something in your presentation that really resonated with me, which was. So I actually, I guess I am a part time product manager right now. But that’s just because, you know, it’s just still, we’re sort of, even though after many, many years still sort of in startup mode, and really helping to relinquish that responsibility at some point. And I think Patrick’s here somewhere. So one of the things that you said, and by the way, the product management part of my job is probably my favourite part, I probably like that more than anything else. But you said something during a presentation, which I really liked, which was, the company is now your product. So and that resonates with me, because that’s actually some of the things that we’ve been doing over the past six months and kind of makes me still feel like a product manager even I’m giving up. But so my question actually is different. So when you’re talking, there was a slide that you showed on general skills. Jackson, and one of the must haves was excellent communication, of course. Yeah. But that one of the bonuses was create designs. And one of the things in my experience, the best way to communicate something an idea to development team, is actually through through markups through markup designs. And actually, I love balsamic and other policymakers in the community. Paleo is really one of the best tools of all time, because it’s a quick way to get ideas on paper. And I feel like well, two things. One, it’s a great way before you present it and refine the idea, because you can kind of go through it very quickly. But then you could hand development team 100 page, spec doc, and then pretty much guarantees that it won’t be read. Or you can do a presentation with markups, which, you know, it was very, very engaging. So sorry for the long question. But my question is, when you said creates designs, did you mean, what did you mean by creates designer seemed like, that was a bonus, where I almost think that that’s a core way to communicate. So it was kind of, you know,

Tim Wilkinson 

I think there’s probably yeah, there’s a couple of different sort of Fidelity’s to that. And again, so in the in the skills matrix, at the bottom, I’ve put in what I call skills, biases. So so depending on depending on what the business needs you, you might want somebody to be aware of all those things in capable all of those directions, but but have a particular depth in one of them. I think it’s but I think there’s a couple of things, I agree with you completely around around being able to communicate visually, I think that is that is so important. And I And again, so I think the point that you’re hiring a product person, you should probably be if you haven’t already hiring a UX or UI type person and product designer type person as well. Because it’s such a such a critical skill that is often not valued enough, actually, I think in in, in early stage companies, and it comes back to bite them later on later on down the line. And the reason why I think that’s important, because then as a PM, you probably shouldn’t be spending lots of time in like sketch or figma, doing high fidelity designs for engineering to implement. But But I think well, you should be able to do exactly the things you’re talking about, which is, you know, communicate, tell stories, and and be able to pick up a pen and scribble on a whiteboard. And actually the good old days of in person interviews, that was one of the things that I always looked for in PMS was you know, we would do and we would do an exercise in a room with a whiteboard. And I would sit and wait for the person to pick up the pen themselves and go to the whiteboard and start Oh, this is what I’m thinking about, you know, really excited, communicating and unable to articulate visually what they’re what they’re kind of thinking about what they’re talking about. And now actually use envision for that kind of thing which is similar to balsamic. They have a product called freehand which is funny to those of us who are old enough to remember Macromedia. But so they have problems with freehand which which you can which is basically like a whiteboard. And it’s and so I do like to try and have a part of the interview process where I can see somebody drawing and articulating their idea is visually boom. So it’s a bit of a rambling answer, Joe. But I guess my point is, I don’t think there’s a lot of value in a product manager, as I say, being able to create design systems, or really get into the weeds of a sketch, you know, you know, high fidelity, work for engineers to then implement. If they are doing that, then I would be concerned. But, but they do need to be able to communicate, and they need some awareness of those kinds of things as well. Obviously, they need awareness of the whole process, and they can help manage it and support the team.

Mark Littlewood 

Great, any other questions before we wrap up?

Tim Wilkinson 

I was one. Sorry. There was one question. So the first question was a double party, I can’t remember who asked it. And the second question was, what are the flags you should look out for? In the first kind of, you know, three months, six months a year? If somebody isn’t if somebody isn’t working out? And I just want to answer it? Because I think it’s a, it’s a really, it’s a really good question. So there are there’s a number of skills, we talked about our communication that are frustratingly called soft skills, because actually, I think they’re the hardest skills in product management, around communicating around leadership around persuasion around credibility. And so I think it’s, if you start to see around ownership, I think if you start to see challenges in those areas, I think those are those, for me are kind of a warning signs. I think one of the first jobs as a pm when they join is to start building that credibility, being able to influence and, and kind of take the team with, obviously, with with kind of humility and empathy. And I think, if If those things aren’t, if those things aren’t happening, then that’s a challenge. And actually, if they if I haven’t managed to do that within sort of three to five months, then they’re probably never going to do it. And then and then the other thing is just if, you know, I mean, that’s it’s common across all roles, but but if if if they just not delivering is the other thing, so if you’re just starting to see that, actually, I mean, obviously things things go south, but But if, if it’s regularly kind of cropping up, that things aren’t happening, things aren’t delivering their excuses. I think that’s a that’s a challenge as well. Those are I mean, it’s honestly, it’s, I’m always nervous to generalise but those are kind of some of the things that I would look out for.

Mark Littlewood 

Great, thank you and really helpful worksheet as well. Don’t, you are able to view only so to Abed not, this is obvious, but save your own copy, so that you don’t mess it up for everybody. And leave your notes about someone to then get cloned across the world. Thank you, Tim. Really, super helpful. And I really liked the question and it was Joe pitch who’s Yeah, in danger of being sent a shiny apple as a teacher’s pet and, and smart questions of the day. But it was talking about you know, how you compensate a set compensation for product people. And this is a meant a lot of the things that we talked about in this session and Lucy’s bear in standalone sessions on their, on their own, but actually rich Marin of has got a lot of things to say about this. And when it comes to Cambridge, for BoS Europe to get away, I just beautifully segwayed in a little plug. So he’s coming to BoS Europe this year for the Cambridge event. And literally his talk is about race resolving the fundamental conflict between product people and everybody that’s forward looking in a business and sales, marketing and everything else, which is really about meeting the next quarter’s numbers. And, yeah, there’s a there’s a lot. There’s a fundamental, there’s a fundamental challenge and wherever you sit in a company, you’re either one or the other and being, you have two completely different sets of language. How do you how do you reconcile it and he’s got some quite provocative thoughts on that. So that’s gonna be great. All right.


Tim Wilkinson

Founder, Product Heads

Tim has developed software products for governments around the world and held senior product leadership positions in some of the UK’s fastest growing startups. 

He founded Product Heads in response to huge challenges that he saw amongst early stage SaaS companies in starting, building and training their product teams to deliver highly valuable, scalable products in the extremely competitive and pressurised world of SaaS companies including Bridebook, Glean, Gravity Sketch, Intelligens as well as organisations including Oxford University, the United Nations and the German Government.


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